1H-pyrrole-2-carbothioamide | 37488-45-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1H-pyrrole-2-carbothioamide
• CAS: 37488-45-2
• 化学式: C₅H₆N₂S
• 分子量: 126.182
• InChiKey: KJEMJZMJDZLKRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  73.9
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1H-pyrrole-2-carbothioamide 在 正丁基锂 、 乙酸酐 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 8.5h， 生成 2-(1'H-pyrrol-2'-yl)thiazole-5-carbaldehyde
  参考文献：
  名称：

  21,23-Dithia-3,13-diazaporphycenes − Novel Aromatic Porphycene Analogues Incorporating Thiazole

  摘要：

  DOI：

  10.1002/1099-0690(200007)2000:13<2449::aid-ejoc2449>3.3.co;2-6
• 作为产物：
  描述：

  1H-吡咯-2-甲酰胺 在 劳森试剂 作用下， 以 四氢呋喃 为溶剂， 反应 13.0h， 以100%的产率得到1H-pyrrole-2-carbothioamide
  参考文献：
  名称：

  Identification and Optimization of Novel Small-Molecule Cas9 Inhibitors by Cell-Based High-Throughput Screening

  摘要：

  DOI：

  10.1021/acs.jmedchem.1c01834

文献信息

• Aerobic Visible‐Light Induced Intermolecular S−N Bond Construction: Synthesis of 1,2,4‐Thiadiazoles from Thioamides under Photosensitizer‐Free Conditions
  作者：Liang Zhuo、Shihua Xie、Hui Wang、Hongjun Zhu

  DOI：10.1002/ejoc.202100440

  日期：2021.6.21

  A green approach for S−N construction with concomitant synthesis of1,2,4-thiadiazoles was developed by visible-light induced oxidative cyclization of thioamides under photosensitizer-free conditions.

  在无光敏剂的条件下，通过可见光诱导硫代酰胺的氧化环化，开发了一种伴随合成 1,2,4-噻二唑的 S-N 构建的绿色方法。
• Regioselective synthesis of substituted thiazoles <i>via</i> cascade reactions from 3-chlorochromones and thioamides
  作者：Tianzi Dai、Chen Cui、Xueyu Qi、Yanshu Cheng、Qian He、Xiaofei Zhang、Xiaomin Luo、Chunhao Yang

  DOI：10.1039/d0ob01019g

  日期：——

  substituted thiazoles via a cascade reaction from chromone derivatives and thioamides in an environmentally benign medium was developed. This cascade reaction involves a Michael addition/intramolecular cyclization process and a broad scope of reversed regioselectivity products was prepared in a short reaction time with excellent yields. The reversed regioselectivity was also explained by DFT calculations

  开发了一种在环境友好的介质中通过色酮衍生物和硫代酰胺的级联反应合成取代噻唑的简便有效的策略。这种级联反应涉及迈克尔加成/分子内环化过程，并且在很短的反应时间内以优异的收率制备了范围广泛的反向区域选择性产物。DFT 计算也解释了反向的区域选择性。
• Synthesis and platelet aggregation inhibitory activity of diphenylazole derivatives. I. Thiazole and imidazole derivatives.
  作者：Norihiko SEKO、Kohichiro YOSHINO、Koichi YOKOTA、Goro TSUKAMOTO

  DOI：10.1248/cpb.39.651

  日期：——

  Diphenylimidazole and diphenylthiazole derivatives were synthesized and tested as inhibitors of platelet aggregation in in vitro experiments with the rabbit. Diphenylthiazole derivatives (10) were more potent than diphenylimidazole derivatives (4) in inhibiting arachidonic acid-induced platelet aggregation of rabbit platelet-rich plasma. Two diphenylimidazole and eight diphenylthiazole derivatives were evaluated for ex vivo arachidonic acid and collagen-induced platelet aggregation inhibitory activity using guinea pigs. In these compounds, 4, 5-bis(4-methoxyphenyl)-2-(1, 5-dimethyl-2-pyrrolyl)thiazole (10n) showed strong activity in vitro and ex vivo. The ex vivo activity of 10n was 200 times stronger than that of aspirin. The mechanism of the activity of 10n was the inhibition of cyclo-oxygenase.

  合成了二苯基咪唑和二苯基噻唑衍生物，并在兔子的体外实验中将其作为血小板聚集抑制剂进行了测试。在抑制花生四烯酸诱导的兔子富血小板血浆血小板聚集方面，二苯基噻唑衍生物（10）比二苯基咪唑衍生物（4）更有效。用豚鼠评估了两种二苯基咪唑和八种二苯基噻唑衍生物对花生四烯酸和胶原蛋白诱导的血小板聚集的体内外抑制活性。在这些化合物中，4, 5-双（4-甲氧基苯基）-2-（1, 5-二甲基-2-吡咯基）噻唑（10n）在体外和体内均表现出很强的活性。10n 的体内外活性比阿司匹林强 200 倍。10n 的活性机制是抑制环氧化酶。
• Novel 4,5-Bis (4-methoxyphenyl)-2-(pyrrol-2-yl) thiazoles and
  申请人：Kanebo, Ltd.

  公开号：US04659726A1

  公开（公告）日：1987-04-21

  Novel 4,5-bis(4-methoxyphenyl)-2-(pyrrol-2-yl)-thiazoles of the formula: ##STR1## wherein R.sup.1 is C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, 2,2,2-trifluoroethyl, a group of the formula: --CH.sub.2 COOR.sup.2 R.sup.2 is C.sub.1-8 alkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, or phenyl-C.sub.1-2 alkyl), or a group of the formula: --(CH.sub.2).sub.n --A--R.sup.3 (A is oxygen or sulfur, R.sup.3 is C.sub.1-4 alkyl or C.sub.2-4 alkenyl, and n is 1, 2 or 3), a process for the preparation of the compounds, and a pharmaceutical composition useful as a platelet aggregation inhibitor which comprises as an active ingredient the above 4,5-bis(4-methoxyphenyl)-2-(pyrrol-2-yl)thiazole compound in admixture with a conventional pharmaceutically acceptable carrier or diluent.

  化合物名称为4,5-双(4-甲氧基苯基)-2-(吡咯-2-基)-噻唑，化学式为：##STR1## 其中R.sup.1为C.sub.1-4烷基，C.sub.2-4烯基，C.sub.2-4炔基，2,2,2-三氟乙基，一个公式为：--CH.sub.2COOR.sup.2的基团R.sup.2为C.sub.1-8烷基，C.sub.2-4烯基，C.sub.2-4炔基，或苯基-C.sub.1-2烷基)，或一个公式为：--(CH.sub.2).sub.n--A--R.sup.3（其中A为氧或硫，R.sup.3为C.sub.1-4烷基或C.sub.2-4烯基，n为1、2或3），制备该化合物的方法，以及一种制剂，其作为血小板聚集抑制剂，包含上述4,5-双(4-甲氧基苯基)-2-(吡咯-2-基)噻唑化合物作为活性成分，与常规的药用载体或稀释剂混合。
• A Practical Synthesis of 3,4-Diethoxybenzthioamide Based on Friedel–Crafts Reaction with Potassium Thiocyanate in Methanesulfonic Acid
  作者：Shinji Aki、Takafumi Fujioka、Masashi Ishigami、Jun-ichi Minamikawa

  DOI：10.1016/s0960-894x(02)00398-0

  日期：2002.9

  The synthesis of 3,4-diethoxybenzthioamide, the key intermediate for OPC-6535, is achieved by employing Friedel-Crafts reaction of 1,2-diethoxybenzene with potassium thiocyanate in methanesulfonic acid at ambient temperature. (C) 2002 Elsevier Science Ltd. All rights reserved.